1,3-Dichloroacetone → HCID 68503221, compound

HRID 1710776Notes

Reaction equation

HRID 1710776 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[C:8]([F:15])[CH:7]=1.[Cl:16][CH2:17][C:18]([CH2:20]Cl)=O>C(#N)CC>[Cl:16][CH2:17][C:18]1[N:12]=[C:10]([C:9]2[CH:13]=[CH:14][C:6]([O:5][CH2:4][CH2:3][CH2:2][Cl:1])=[CH:7][C:8]=2[F:15])[O:11][CH:20]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 59457468HCID 59457468, compound

Product 1

HCID 68503221HCID 68503221, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(3-chloropropoxy)-2-fluorobenzamide i82 (0.41 g, 1.75 mmol, 1 eq) and 1,3-dichloroacetone (0.49 g, 3.85 mmol, 2.2 eq) in propionitrile (9 ml) is stirred at 100° C. for 60 h. The mixture is then concentrated under vacuum, taken up in dichloromethane, and washed with water. The organic phase is dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography over silicagel (eluent: dichloromethane) to afford 0.23 g of 4-(chloromethyl)-2-[4-(3-chloropropoxy)-2-fluorophenyl]-1,3-oxazole i84.

Workup

  1. concentrationThe mixture is then concentrated under vacuum
  2. washwashed with water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by chromatography over silicagel (eluent: dichloromethane)

Sources & evidence

ORD record
ord-27f1f66004f9426986bd62f9d4852ae5
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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